Lipstatin | CAS#96829-59-3 | pancreas lipase inhibitor

MedKoo Cat#: 597474 | Name: Lipstatin

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Lipstatin is a potent inhibitor of the pancreas lipase, is reported to be useful in the treatment and/or prevention of obesity and related diseases.

Chemical Structure

Lipstatin

CAS#96829-59-3

Theoretical Analysis

MedKoo Cat#: 597474

Name: Lipstatin

CAS#: 96829-59-3

Chemical Formula: C29H49NO5

Exact Mass: 491.3611

Molecular Weight: 491.71

Elemental Analysis: C, 70.84; H, 10.04; N, 2.85; O, 16.27

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Synonym

Lipstatin;

IUPAC/Chemical Name

(2S,4Z,7Z)-1-((3R)-3-hexyl-4-oxooxetan-2-yl)trideca-4,7-dien-2-yl formyl-L-leucinate

InChi Key

OQMAKWGYQLJJIA-AKFWTAMJSA-N

InChi Code

InChI=1S/C29H49NO5/c1-5-7-9-11-12-13-14-15-16-18-24(34-29(33)26(30-22-31)20-23(3)4)21-27-25(28(32)35-27)19-17-10-8-6-2/h12-13,15-16,22-27H,5-11,14,17-21H2,1-4H3,(H,30,31)/b13-12-,16-15-/t24-,25+,26-,27?/m0/s1

SMILES Code

CC(C)C[C@@H](C(O[C@H](CC([C@H]1CCCCCC)OC1=O)C/C=C\C/C=C\CCCCC)=O)NC=O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.03.00

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Lipstatin is a potent inhibitor of the pancreas lipase.

In vitro activity:

TBD

In vivo activity:

Lipstatin contains a beta-lactone structure that probably accounts for the irreversible lipase inhibition. The IC50 of lipstatin for pancreatic lipase is 0.14 microM. In mice triolein absorption was dose-dependently inhibited by lipstatin, whereas oleic acid was absorbed normally. Reference: J Antibiot (Tokyo). 1987 Aug;40(8):1081-5. https://pubmed.ncbi.nlm.nih.gov/3680018/

Preparing Stock Solutions

The following data is based on the product molecular weight 491.71 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Weibel EK, Hadvary P, Hochuli E, Kupfer E, Lengsfeld H. Lipstatin, an inhibitor of pancreatic lipase, produced by Streptomyces toxytricini. I. Producing organism, fermentation, isolation and biological activity. J Antibiot (Tokyo). 1987 Aug;40(8):1081-5. doi: 10.7164/antibiotics.40.1081. PMID: 3680018.

In vitro protocol:

TBD

In vivo protocol:

1: Zhu T, Wang L, Wang W, Hu Z, Yu M, Wang K, Cui Z. Enhanced production of lipstatin from Streptomyces toxytricini by optimizing fermentation conditions and medium. J Gen Appl Microbiol. 2014;60(3):106-11. PubMed PMID: 25008166. 2: Bai T, Zhang D, Lin S, Long Q, Wang Y, Ou H, Kang Q, Deng Z, Liu W, Tao M. Operon for biosynthesis of lipstatin, the Beta-lactone inhibitor of human pancreatic lipase. Appl Environ Microbiol. 2014 Dec;80(24):7473-83. doi: 10.1128/AEM.01765-14. Epub 2014 Sep 19. PubMed PMID: 25239907; PubMed Central PMCID: PMC4249243. 3: Kumar P, Dubey KK. Modulation of fatty acid metabolism and tricarboxylic acid cycle to enhance the lipstatin production through medium engineering in Streptomyces toxytricini. Bioresour Technol. 2016 Aug;213:64-68. doi: 10.1016/j.biortech.2016.01.133. Epub 2016 Feb 11. PubMed PMID: 26897471. 4: Demirev AV, Khanal A, Sedai BR, Lim SK, Na MK, Nam DH. The role of acyl-coenzyme A carboxylase complex in lipstatin biosynthesis of Streptomyces toxytricini. Appl Microbiol Biotechnol. 2010 Jul;87(3):1129-39. doi: 10.1007/s00253-010-2587-2. Epub 2010 May 2. PubMed PMID: 20437235; PubMed Central PMCID: PMC2886142. 5: Schuhr CA, Eisenreich W, Goese M, Stohler P, Weber W, Kupfer E, Bacher A. Biosynthetic precursors of the lipase inhibitor lipstatin. J Org Chem. 2002 Apr 5;67(7):2257-62. PubMed PMID: 11925237. 6: Ngai MH, Yang PY, Liu K, Shen Y, Wenk MR, Yao SQ, Lear MJ. Click-based synthesis and proteomic profiling of lipstatin analogues. Chem Commun (Camb). 2010 Nov 28;46(44):8335-7. doi: 10.1039/c0cc01276a. Epub 2010 Jun 24. PubMed PMID: 20577697. 7: Weibel EK, Hadvary P, Hochuli E, Kupfer E, Lengsfeld H. Lipstatin, an inhibitor of pancreatic lipase, produced by Streptomyces toxytricini. I. Producing organism, fermentation, isolation and biological activity. J Antibiot (Tokyo). 1987 Aug;40(8):1081-5. PubMed PMID: 3680018. 8: Eisenreich W, Kupfer E, Weber W, Bacher A. Tracer studies with crude U-13C-lipid mixtures. Biosynthesis of the lipase inhibitor lipstatin. J Biol Chem. 1997 Jan 10;272(2):867-74. PubMed PMID: 8995375. 9: Goese M, Eisenreich W, Kupfer E, Weber W, Bacher A. Biosynthetic origin of hydrogen atoms in the lipase inhibitor lipstatin. J Biol Chem. 2000 Jul 14;275(28):21192-6. PubMed PMID: 10801870. 10: Goese M, Eisenreich W, Kupfer E, Stohler P, Weber W, Leuenberger HG, Bacher A. Biosynthesis of lipstatin. Incorporation of multiply deuterium-labeled (5Z,8Z)-tetradeca-5,8-dienoic acid and octanoic acid. J Org Chem. 2001 Jun 29;66(13):4673-8. PubMed PMID: 11421791. 11: Hochuli E, Kupfer E, Maurer R, Meister W, Mercadal Y, Schmidt K. Lipstatin, an inhibitor of pancreatic lipase, produced by Streptomyces toxytricini. II. Chemistry and structure elucidation. J Antibiot (Tokyo). 1987 Aug;40(8):1086-91. PubMed PMID: 3680019. 12: Eisenreich W, Kupfer E, Stohler P, Weber W, Bacher A. Biosynthetic origin of a branched chain analogue of the lipase inhibitor, lipstatin. J Med Chem. 2003 Sep 11;46(19):4209-12. PubMed PMID: 12954074. 13: He D, Huang L, Xu Y, Pan X, Liu L. Computational analysis and enzyme assay of inhibitor response to disease single nucleotide polymorphisms (SNPs) in lipoprotein lipase. J Bioinform Comput Biol. 2016 Oct;14(5):1650028. Epub 2016 Jun 26. PubMed PMID: 27427383. 14: Yoo A, Demirev AV, Lee JS, Kim SD, Nam DH. Cloning and analysis of a type II polyketide synthase gene cluster from Streptomyces toxytricini NRRL 15,443. J Microbiol. 2006 Dec;44(6):649-54. PubMed PMID: 17205043. 15: Nakai K, Wada R, Iida S, Kawanishi T, Matsumoto Y. Modeling and simulation of orlistat to predict weight loss and weight maintenance in obesity patients. Drug Metab Pharmacokinet. 2014;29(3):278-82. Epub 2014 Jan 14. PubMed PMID: 24418823. 16: Borgström B. Mode of action of tetrahydrolipstatin: a derivative of the naturally occurring lipase inhibitor lipstatin. Biochim Biophys Acta. 1988 Oct 14;962(3):308-16. PubMed PMID: 3167082. 17: Demirev AV, Khanal A, Hanh NP, Nam KT, Nam DH. Biochemical characteristization of propionyl-coenzyme a carboxylase complex of Streptomyces toxytricini. J Microbiol. 2011 Jun;49(3):407-12. doi: 10.1007/s12275-011-1122-1. Epub 2011 Jun 30. PubMed PMID: 21717326. 18: Híreš M, Rapavá N, Šimkovič M, Varečka Ľ, Berkeš D, Kryštofová S. Development and Optimization of a High-Throughput Screening Assay for Rapid Evaluation of Lipstatin Production by Streptomyces Strains. Curr Microbiol. 2018 May;75(5):580-587. doi: 10.1007/s00284-017-1420-x. Epub 2017 Dec 18. PubMed PMID: 29256008. 19: Kumar P, Dubey KK. Implication of mutagenesis and precursor supplementation towards the enhancement of lipstatin (an antiobesity agent) biosynthesis through submerged fermentation using Streptomyces toxytricini. 3 Biotech. 2018 Jan;8(1):29. doi: 10.1007/s13205-017-1049-2. Epub 2017 Dec 26. PubMed PMID: 29291142; PubMed Central PMCID: PMC5742565. 20: Quah SY, Tan MS, Teh YH, Stanslas J. Pharmacological modulation of oncogenic Ras by natural products and their derivatives: Renewed hope in the discovery of novel anti-Ras drugs. Pharmacol Ther. 2016 Jun;162:35-57. doi: 10.1016/j.pharmthera.2016.03.010. Epub 2016 Mar 22. Review. PubMed PMID: 27016467.